Trip Planning

With so many opportunities to hike, paddle, and bike your way through Chesapeake, VA, the questions of where to begin and what to do next can start to feel daunting. But no worries—you’ve come to the right place! Our trip planning resources are like a seasoned kayaking guide, helping you navigate through the canals of planning your trip to Chesapeake to make informed decisions on how to spend your time in this fantastic region.

Plan With Confidence

For some visitors, a complete list of activities, restaurants, and photos of the surrounding sights is exactly what’s needed to start realizing the potential of a place. If this sounds like you, head over to our free Visitor’s Guide and fill out a short form to quickly receive a hardcopy of the official Chesapeake Visitor Guide by mail. While you’re there, let us know if you’re a history buff, a shopaholic, or someone who is more at home in the outdoors while fishing and camping, and we’ll deliver content to your inbox that is tailored to your interests.

If you are already on your way to Chesapeake, have no fear because the Visitor Center is here. Come on in and feel free to flip through pamphlets to learn about the best places for stand-up paddleboarding, camping, or dining out. And if you prefer a general overview of the area, check out our Coastal Virginia section to learn a bit more about what makes this area a must-see.

Travel Resources

Whether you are flying in, taking the bus, or coming in by rail, we have maps and transportation information to help you. If you need a phone number, address, or other forms of contact with one of the four airports in the region, or a bus or train schedule, search no further.

And, while the saying goes, “you can plan a pretty picnic, but you can’t predict the weather,” you can at least get a good idea of what to pack by checking out our weather section. Chesapeake has four distinct seasons throughout the year, but locals love the wonderfully mild summers and winters.

Trip Ideas

Now, let’s say you’re the type of person who wants to dive a little deeper into learning what the people and places are like where you’ll be going before you arrive. The Chesapeake Uncovered blog will fill your mind with insider information about the sights and sounds in the region. You’ll read first-hand experiences during the annual Restaurant Week when local restaurants showcase their culinary prowess in special menus for a set price. There are also posts about the best places to visit during certain seasons or upcoming festivals on the horizon.

If you prefer a bit more of a preplanned approach, read through trip ideas and see if one of the itineraries strikes your fancy. There are ideas suited for couples, adventure seekers, and those who like to sip their way into an area via wine tours. We also suggest you sign up for our digital newsletter for exciting news whether you’re visiting Chesapeake for the first time or returning for a homecoming. And if you have any questions, comments, or suggestions, please contact us at any time.